Ethyl Acetate → HCID 178501522, compound

HRID 2279134Notes

Reaction equation

HRID 2279134 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:29])[CH:5]=[CH:6][C:7]=1[C:8]1[N:13]=[C:12]2[NH:14][N:15]=[C:16]([CH3:17])[C:11]2=[C:10]([CH2:18][N:19]2[CH2:24][C:23]([CH3:26])([CH3:25])[NH:22][CH2:21][C:20]2([CH3:28])[CH3:27])[CH:9]=1.CCN(C(C)C)C(C)C.Br[CH2:40][C:41]([O:43][CH3:44])=[O:42].C(OCC)(=O)C>C1COCC1.O>[CH3:44][O:43][C:41](=[O:42])[CH2:40][N:22]1[CH2:21][C:20]([CH3:28])([CH3:27])[N:19]([CH2:18][C:10]2[CH:9]=[C:8]([C:7]3[CH:6]=[CH:5][C:4]([OH:29])=[CH:3][C:2]=3[F:1])[N:13]=[C:12]3[NH:14][N:15]=[C:16]([CH3:17])[C:11]=23)[CH2:24][C:23]1([CH3:25])[CH3:26]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 178434404HCID 178434404, compound

Product 1

HCID 178501522HCID 178501522, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 30 mg of 3-fluoro-4-[3-methyl-4-(2,2,5,5-tetramethyl-piperazin-1-ylmethyl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-phenol in 1 ml of dry THF were added 13 mg of DIPEA and 11 mg of methyl bromoacetate. The reaction was stirred at r.t. for 2 h and then heated in a microwave reactor for 3 h at 120° C. Then ethyl acetate and water were added and the pH was adjusted to 7-8. The phases were separated and the aqueous phase was extracted with ethyl acetate twice. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. After purification by preparative HPLC (C18 column, acetonitrile/water gradient) 12 mg (37%) of the title compound were obtained.

Workup

  1. temperatureheated in a microwave reactor for 3 h at 120° C
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate twice
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customAfter purification by preparative HPLC (C18 column, acetonitrile/water gradient) 12 mg (37%) of the title compound
  8. customwere obtained

Sources & evidence

ORD record
ord-7611617f1d724a878b80cffa57b2a812
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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